I am able to access a shared library, but can't figure out how to sync with my ipod

My son got a new laptop for Christmas. I set up his itunes acct and he lost most songs that were on his ipod. They are in my library so I have set up home shareing. I can access my library in his itunes account, but can't figure how to sync that library to his ipod. When I do click sync, it only syncs a couple of songs that are already on his ipod.
I've tried highlighting all songs and dragging to "hisipod", but they will not drag.

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I am able to access a shared library, but can't figure out how to sync with my ipod

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